Sodium Bicarbonate → HCID 59252823, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 5-(hydroxy(phenyl)methyl)-N,N-dimethyl-1H-indole-1-carboxamide (0.72 g, 2.5 mmol) and (1-methoxy-2-methylprop-1-enyloxy)trimethylsilane (8 mL) in anhydrous dichloromethane (6 mL) was added boron trifluoride diethyl ether complex (0.83 mL, 6.6 mmol) dropwise at 0° C. under argon. After stirring at 0° C. for 30 min and rt for 3.5 hr, the mixture was poured into a saturated aqueous sodium bicarbonate solution maintained at 0° C. The reaction mixture was stirred well, extracted with ethyl acetate (20 mL), dried (Na2SO4) and concentrated. Silica gel flash chromatography gave methyl 3-(1-(dimethylcarbamoyl)-1H-indol-5-yl)-2,2-dimethyl-3-phenylpropanoate (0.9 g, 2.4 mmol, 96% yield) as a glassy solid, the NMR spectrum of which was consistent with the desired structure.

Provenance & Evidence